Play The Game Tonight
by GirlWhoLovesJensen
Summary: I finally found a title for the story. It is a name of a Kansas song and it just seems to fit. Later you will understand why it fits, you will just have to read to find out.
1. Chapter 1

"How the hell did I get myself into this?" Skyler asked herself, "I've only been in Italy for a couple of months and I've already gotten mixed up in something." The gun she had put in the back of her pants was getting uncomfortable so she took it out and set it beside her on the tan seat of the car that was racing down the winding road. She turned to face the window and watched the misty Italian night pass her reflection as she thought back on the events that brought her to the backseat of the speeding Impala.

It all started a week before when she had first noticed the two guys. It wasn't that hard to spot them because they stood out of the crowd of fashionably dressed Italians and brightly colored tourists milling around in the square. She had immediately noticed their dingy, earth-toned clothes that one could possibly call stylish. Also one of them was carrying some kind of FM radio with headphones plugged into it. The radio wouldn't have been something strange, except the guy was waving it from side to side as he walked along and it wasn't the kind of moving along to a song kind of thing it was more like you would move a metal detector, as if he were searching for something. She sat there in the café, chin in her hand, watching them. She saw their every move, every step that they took, every person they talked to, and she was entranced by them. Her grey-blue eyes followed them around the square until she lost them in the lunch time crowd.

Skyler walked back to her apartment later that day in a daze. She couldn't focus and she felt like she was in a haze. All she could think about were those two strange, yet gorgeous, guys she had seen in the square. There was something about them that she couldn't quite put her finger on, but it was there. She decided to take it upon herself to find out what they were doing. She sat up half the night on her couch, staring out the window watching the moon until she fell asleep. Even her dreams were haunted by those boys.

The next morning she woke up and dragged her weary body to the café so she could watch for those two guys again. She sat in her usual seat at her usual table; making things seen like a usual day, but really her sense were tingling and alert. She looked and listened for anything that might give her a clue as to where those guys were. She sat drinking her latte and was startled when she actually saw them walk into the café, and they weren't alone. Accompanying them was her neighbor's, or should she say ex-neighbor's, boyfriend, John. He had dated Kira, the girl who had lived in the apartment next to Skyler's, until Kira died mysteriously a few days ago, found in her apartment, apparently murdered. She couldn't for the life of her figure out what John was doing with these guys; they weren't the kind of people he normally hung out with. John was a soft and cuddly guy and these two guys were so rough and hardened, it seemed weird that he was with them. Skyler watched them over the rim of her latte, "They just keep getting more and more interesting," she thought as she watched them leave, leaving a stunned looking John in their wake.


	2. Chapter 2

This whole thing went on for a few days. Skyler would go to the café and sit in her chair, waiting for those two fascinating guys. Then they would come in, with a new person everyday. One day, after they had brought in the mother of one of the people killed in her apartment building, she snapped. She stood up and rushed past the two mystery men, running into one of them. She quickly made her way across the square and to her apartment, slamming the door behind her as she reached her room. She began pacing the room, racking her brain for any sane reason for those men to be talking to all of these people, but she couldn't figure it out and it was driving her completely insane. Just sitting quietly and watching them wasn't enough, she wanted the big picture and what she was doing now was only giving her a part of that picture. She wanted it all so she decided that she would just have to move on to a more drastic method of observation, she was going to have to follow them.

* * *

Dean and Sam had flown into Italy one week ago. This was probably the biggest hunt that they had ever been on, considering that they had left the country, forcing Dean to face his fear of flying. But fly they did and many stressful hours later they landed in Italy in one piece, although Sam practically had to pry Dean's hands off of the arm rest of the airplane seat. They started off by using Dean's homemade EMF detector, fashioned out of an old radio, to search the area for anything supernatural. Then, they moved on to finding people connected to the murder victims. When they found someone they would pull out the fake I.D.'s or come up with some crazy story about how they knew that person and then they would begin asking questions. There had been about five total murders in the area within one month. Normally this would go unnoticed by the Winchester boys, but the murders were unusual for the area, plus, there had been a strange lull in the supernatural and paranormal activity back in the states and they were bored. Of course there was always a murder or two in the area, but there had never been five in one month where the victims had been beheaded, like they used to in medieval times. So the boys came to Italy, for not only what might be the hunt of their lives, but for a change of scenery. The same old places, time after time, were beginning to get old and they needed something new.

By the time Dean had noticed the girl he and Sam had interviewed almost three people. Every time they stepped into the little café in the square she was there, watching them with the most intense eyes he had ever seen, her grey-blue eyes focused on their every move like her life depended on it. On the day that they had lunch with the mother of one of the murder victims she was there again, waiting. Her eyes followed them as they walked in and when she spotted the woman trailing behind them her eyes flew open with surprise and her jaw dropped. She stood up quickly and walked briskly past them. Dean watched her as she stormed off through the square, shoving people out of her way, and heading straight for an apartment building, the same one where all of the murders were happening.

After Dean and Sam finished talking to the woman, Dean still couldn't figure out what they were looking for, so he decided that they would just have to call in a fellow hunter for some help.

"Sam, give me your phone." He asked, ever so politely.

"Why do you need it?" Sam asked shortly.

"Because idiot, I'm calling Jo. I think we may need some help on this one."

Dean took the phone from his moody brother's outstretched hand and dialed Jo's number. As it was ringing Dean looked at his brother and said seriously, "It must be Thursday Sam."

"Why?" Sam asked with a puzzled expression on his face.

"Because, you're angsting." Dean said, still holding his serious expression. Suddenly, he heard a click on the line and Jo's voice saying hello. "Hey Jo it's Dean. Listen, we need your help." He paused for a moment. "We're on a job, but we're having some issues figuring out what the hell we're dealing with. We're in Italy, have been for a few days, and we've been investigating a string of murders, all exactly the same. All of the people lived alone, all of them in the same apartment building, and all of them had their heads chopped off." He was quiet for a moment, letting what he had just said to Jo sink in. "O.K. Sam will be at the airport to pick you up tomorrow." He closed the phone and handed it to Sam.

"So Jo is coming?" Sam asked Dean. Sam liked Jo, she was nice, intense, but nice, but ever since she had found out about Sam and Dean's dad accidentally getting her dad killed Jo was a little more intense than usual.

"Yes, she is coming, and you are going to pick her up."

"Why me?" Sam asked pitifully.

"Because she likes you better." Dean answered, turning his back on Sam.

Sam stood motionless for a moment, pouting, and then he said quietly, "Fine. Jerk."

Dean casually turned to face his brother, a smirk on his face, and then he replied, "Bitch."


	3. Chapter 3

The next day Skyler went to the café and sat as calmly as she could, waiting for her mystery men. She sat there for half an hour, wondering if they were ever going to show up, when suddenly, out of the corner of her eye she saw a flash of black and denim, it was them. They were moving quickly across the square and she didn't want to lose them so she stood up, grabbed her purse, left her latte, and took off after them. They turned down a back alley to get away from the crowded square and then they slowed down. Skyler had never known how loud her shoes were until she started to walk in that alley, so, knowing she would hate herself for it later, she took off her shoes and continued after them. When they were about halfway down the alley, the guys stopped. Skyler jumped behind the nearest object, which happened to be a dumpster, just in case they came her way again. She peeked around the corner to see what was going on, she didn't want to lose them. She looked just in time to see the shorter one turn to the taller one and say something.

"You go get Jo," she heard the small one say, "I think I'm gonna stay here, it feels like we are being followed."

Skyler saw him hand the big one some car keys just before she ducked back behind the dumpster. She hadn't been that loud, had she? She slowly leaned back around the corner of the dumpster just in time to see the one that had stayed behind start to walk away. She began to come out from behind the dumpster slowly, but as soon as her foot hit the ground, the guy spun around, a gun fixed on her as he turned.

"Now can someone please explain to me what a pretty girl like you is doing following me around?" His eyes were narrowed with suspicion as he continued to look at her. "I know I am nice to look at, but you may not want to get involved with guys like me." He slowly walked towards her, gun still aimed at her as a precaution.

"Well, I don't really know how to put this, so I guess I will just tell you." Skyler hoped that this guy wouldn't believe the truth; he didn't really look like he was extremely bright. "I have been watching you and you friend around for a couple of days now. You two are a little strange and don't really fit in here so I wanted to figure out what was going on." She admitted this with an ashamed tone.

"Well I am flattered, and I'm sure my brother would be, that such a good looking girl is interested in us. I'm still not so sure that you really want to be messing with us. And anyways, stalking and obsessing isn't the best way to get a guy to like you." He lowered the gun and put in the back of his pants when he had decided that she wasn't a threat.

"I am not stalking and I am not obsessing. I am simply following you every where you go and staying out of sight while I follow. And believe me, I am not doing this to get you to like me." She gave him the up and down look as she took in his ensemble. His face was nice, and maybe on some other planet his clothes could be called fashionable, definitely not her type.

"Mmhhmm. Sure. That's what they all say." He responded sarcastically. "Seriously, you don't want to get involved with what is going on here."

"I'm pretty sure I do actually. Five people have died in my apartment building and all of the people that you have talked to have either known them really well or have been related to them." She saw him open his mouth to start to say something, "Don't tell me that it is just a weird coincidence or you are related to them, because I know that that is not true."

"But what if it is true?" he responded innocently.

"Bull shit!" she yelled. "I knew all of these people, I was friends with them, and they never mentioned you or your brother!" she was furious, she couldn't believe that this guy thought that she was stupid enough to believe that crap.

"Geez, someone is a little angry!" Fine, me and Sam don't know any of these people." He turned his back on her and walked away a couple of feet.

Skyler stood there and watched him as he ran his hand through his short hair, a gesture she had seen from many guys who were frustrated with her. "So, are you going to let me help?" She asked quietly, walking around him so she could see his face.

"Fine," he said, clenching his jaw in frustration.


	4. Chapter 4

"How am I going to ditch this girl?" Dean thought to himself. "Or do I _really_ want to ditch her?" he thought again, taking another look at her.

"Well since we are going to be working together, or whatever, I guess we should get to know each other. I will tell you my name and you can tell me yours. Deal?" the annoying girl said, taking a few steps towards him to close the gap between them. "I'm Skyler, but you can call me Skye." She stuck her right hand out in front of herself, waiting for him to do the polite thing and shake it.

"I'm dean, you can call me Dean." He said, briefly shaking her hand and then letting go of it like it was on fire. He glanced at his watch, wondering how long it could possibly take Sam to get to the airport and back. He wasn't sure how much longer he could stay here with this girl. There was something about her that really annoyed him, but there was something underneath that, something that wasn't so bad, but he couldn't quite put his finger on it.

"So what brings you and your brother to Italy?" She asked, breaking the tension of silence between them.

Dean wasn't sure how to respond to that one. Maybe if he told her the truth she would run away screaming, but did he _really_ want her to do that? Yeah, he would just tell her the truth and see what happened. "Well me and Sam are here for our job. Basically what we do is hunt ghosts and spirits and things like that and send them back to hell or where ever they are supposed to go. We think what is going on in your apartment building has something to do with stuff like that."

"So you are like the Ghostbusters?" Skyler asked, looking confused.

"No we are not like the freakin' Ghostbusters. For one, we don't wear jumpsuits and suck ghosts up into vacuum cleaners, that doesn't work."

"And two?"

"What?"

"You said 'for one', that means there has to be a two." She said, looking at him like he was an idiot.

"Fine. And two, umm, we are way better looking than the Ghostbusters." He said disgustedly. Why hadn't the running and screaming happened yet?

"So let me get this straight. You and your brother, Sam, hunt ghosts and things that go bump I the night, and you think that is what is killing the people in my apartment building." A confused expression crossed her face as she looked at him questioningly. "Are you on drugs?"

"That's right, except for the part about me being on drugs." Dean glanced at his watch again. What the hell was taking Sam so long? It had already been half an hour, the airport wasn't that far away. Dean hoped and prayed that Sam would hurry up and get there with Jo so he could just leave, or not leave, Skyler behind. He was still undecided on that front. He started to head towards the place that he and Sam had agreed to meet at and as he walked he heard Skyler's quick footsteps behind him as she tried to put her shoes back on and catch up with his long-legged pace.

"Wait!" he heard her shout. "I'm coming with you!"

Dean didn't slow down much, just enough for her to catch up. "So I've told you why me and my brother are here, why are you here?" he asked, turning a corner and leaving the alley. "You're definitely not Italian, I can tell because of your accent. You are from the U.S., somewhere in the south, South Carolina?"

"Close, but no. I'm actually from Georgia. I'm over here because I was studying fashion, but that didn't work out so well. Going to fashion school took all of the fun out of it so now I am just here, waiting until I get up the courage to go back home and face my parents." Skyler shook her head sadly at her own failure and did not look like she was looking forward to experiencing that encounter with her parents.

"Well that sounds like fun." Dean said dryly. They had stopped walking and were now standing next to a one way street. Dean leaned against a building behind him and crossed his arms. "Sam is going to be here any minute now so if I were you I would hurry up and decide if I were going to get involved in this." Just as he finished speaking a black '67 Chevy Impala came down the street and stopped in front of them. It was the kind of car that If it stopped next to you at a red light you would lock your doors. The window on the driver's side rolled down and Sam leaned out of it to talk to his brother.

"Who is your friend Dean?" he asked.

"This is the person who was following us. Her name is Skyler and apparently she wants in non the hunt."

"You told her about the hunt?" A look of shock spread across Sam's face as he looked at Dean.

"And I kind of told her who we were also." Dean said this with an ashamed look on his face.

"Dean." Sam said with an exasperated sigh and the shocked look that had been on his face was replaced by one of disappointment.

"He never could keep his mouth shut around girls." The blonde figure in the seat next to Sam said this with a "why aren't you surprised" kind of tone.

"Well hi to you too Jo." Dean snapped. "Is it just Pick On Dean Day today, cause it sure as hell feels that way."

Then, Skyler chimed in, 'So where do I sit?" she asked, looking for an open space in the backseat.

Dean looked into the backseat of the car and saw that one half of the backseat had rock salt bags pilled in it. Maybe this girl was one of those delicate fainting kind of girls and the idea of sitting on bags of rock salt would make her go away. "Well if you are going to come with us you are going to have to sit in the back with me." Out of the corner of his eye he caught the questioning look Sam shot him.

"Ok, fine by me." She said, making a move towards the door.

"Hold up Ace." Dean said, stopping her just before she opened the door. "You are sitting on the other side, on the rock salt bags. I'm far to delicate to sit on those." There was a look of complete seriousness on his face and he struggled to keep it there when he heard Sam laughing quietly behind him.

"Mmmhhhmmm. Well it's a good thing I'm not a pansy and can handle the rougher conditions of life." Skyler said as she walked around the car, loud enough for Dean to hear.

Dean stopped halfway through opening the door and at that moment he knew that this hunt was going to be a lot more interesting now that Skyler was along for the ride.


	5. Chapter 5

_Finally I have the long awaited update to one of my stories. This chapter isn't much, but there is something really good coming just around the corner._

* * *

Skyler slid into the backseat of the car and tried to get comfortable atop the bags of rock salt. "So, what exactly are we looking for here? I mean, I know we are going after whatever is killing people in my apartment building, but do you know what it is?" She leaned forward in her seat, trying to take as much of her weight off of the seat as she could, and braced herself on the back of Jo's seat.

"We think it may be demonic possession or some kind of vengeful spirit, but we haven't had much time to do research on local legends since we have been so busy asking people questions." Dean said, trying to do his best to explain.

Sam must have noticed the confused expression on her face because he tried to explain it in simpler terms. "Demonic possession is when a demon gets inside you and takes over while you are just along for the ride, it's not fun." He shuddered inwardly, remembering the time he had been possessed. "A vengeful spirit is pretty much the ghost of some one who died a messy or unfair death and they get angry, but I do believe there are some other kinds."

"Sam you are one of the smartest sounding dumb people I know." Jo said laughing at Sam and the way he talked.

"Wow you are just a walking encyclopedia of weirdness." Skyler said laughing as she began to understand.

"It's been said. " Sam said, looking back at his brother, who was struggling to suppress his laughter.

"Well what are you waiting for college boy? Drive!" Dean said, pulling on a straight face and slapping the back of Sam's seat.

Sam started the Impala back up and started to drive. "So if you are going to really go on this hunt with us then you are going to have to carry a gun or something. We can't just let you walk around without something to protect yourself with."

"Aww cute, he's concerned." Skyler said, laughing at Sam. "Don't worry, I already carry a knife with me in my purse. You never know what one of these people might do if they see a cute purse or pair of shoes."

Dean rolled his eyes and looked at Skyler. "You are going to need more than a knife in your purse in this line of work." It was boot camp time; they were going to have to teach this girl the ropes, just like they had had to do with their sister. Hopefully this girl wouldn't get mad at them for trying to protect her and run off like Alana had done.

Jo turned around in her seat and looked at Skyler. "Well she could either carry a small gun in a holster around her ankle or we could probably find a way for her to carry a small gun under her shirt."

"Gun under the shirt would be kind of obvious on this one." Dean said, giving Skyler the elevator eyes. "But on the ankle would work if you wear jeans."

"Well Dean, we girls are pretty smart, we could probably figure out a way for her to carry a gun under her shirt without it being seen, but on the ankle under jeans would be best, but you could have a knife or something like that to carry when you don't wear jeans, it's not as good as a gun, but it's protection." Jo said, thinking again.

"That works for me. So where are we headed?" Skyler asked. She looked out the car window, trying to find a landmark or something that she recognized to tell her where they were.

"We are going to the hotel that me and Dean have been staying in. It is just a couple more minutes away." Sam said, focusing on the road, trying to maneuver around a biker that was in front of them.

"Dude, the hotels around here rip you off. I have a huge empty apartment and ya'll can come stay with me. It is no problem at all." That second Skyler started thinking about room arrangements and what she would have to move to make room for three more people.

Sam shook his head, declining her offer. "No, really, we can just stay at the hotel."

Dean's jaw dropped as he listened to his brother. "Sam, did you not hear her? She is offering us a free place to stay and you are turning her down? You need to find out who dropped you on the head as a child and sue them, cause there is brain damage my friend."

"Really Sam, it is fine. Anyways, all of the people in my apartment building that have been murdered lived by themselves, so I would rather have my apartment full of people. You know what they say, safety in numbers." Skyler said, hoping that they would take her offer. It was creepy in her apartment when it was just her.

"Are you sure we wouldn't be too much trouble?" Sam asked, a concerned tone in his voice.

"Sam you are too polite for your own good." Jo said shaking her head. "Skyler we would love to come stay with you, thanks for the offer."

Sam stuck his tongue out at Jo as he slid the Impala around the middle aged biker and then he asked, "So where exactly do I need to go to get to your apartment Skye?"

"Well, really you need to be going in the opposite direction." Skyler said.

"Sam when you pull the illegal U-ie that I know that you are about to do, watch out for the other cars. I really don't want you to scratch my car, I am saying this for your own good." Dean braced himself on the armrest next to him and prepared for Sam to whip the car around. Then he caught the weird look that Skyler was giving him. "What?"

"This is your car?" She asked disbelievingly.

"Yeah, what's it to you?"

"Well I was just thinking if I had a car like this I would drive it no matter what." She said quietly.

"We are in traffic though." Dean said, as if that would explain everything.

"And?" Skyler asked, still feeling left in the dark..

Sam sighed and explained for Dean. "Dean doesn't have the patience to drive in traffic."

"Yeah, I would get mad and frustrated and then I would want to hit something. I can't take any chances with this car. I would probably have a panic attack if something happened to it." Dean said, shuddering at the thought.

"I would probably cry if I had this car and something happened to it."

Skyler said, imagining what her reaction would be like.

Sam laughed quietly to himself. "Been there done that."

"Psshhh. I didn't cry Sam, I fixed this beautiful piece of machinery." Dean turned to face Skyler. "A year, year and a half ago, she got hit by a transport. She was completely totaled."

"Wow, so a transport jus hit a parked car, cause there was no way you two could have been in it, you would be all scarred up or dead if you were, or at least vegetables. But hey, you did a good job of fixing it up Dean." Skyler had a look of surprise on her face.

"Well the car wasn't exactly parked." Sam said, not wanting to tell the whole story. "It is kind of a long story."

"No it's not Sam. We were driving to a hospital after fighting the yellow eyed demon when the truck driver became possessed and decided to shmuck us. Apparently I was in, like, a coma, Sam was the only one ok. My dad wasn't banged up too bad, but then he decided to go and sell his soul to the damned demon to save me. I woke up, my dad died. Then I beat up my car some more, had a couple of Sam moments, and then I fixed the car. That's it in a nutshell." Dean had a pained look in his eyes as he told the story. After all this time, what his dad had done for him still bugged him.

Despite the sadness of the story Dean had just told, Jo couldn't help but laugh and add, "And then they came and found my mom and me and stirred up all kinds of trouble."

"Wow, umm, I'm sorry. You two sure have been through a lot. That makes it all seem more real, hearing your story I mean." Skyler said, looking shocked.

"Damn right it's real." Dean said, thinking of all of the things that he had hunted in his lifetime.

"What Dean means to say is yeah it's tough, but if we don't stop things, who will?" He heard Jo clear her throat when he said this, so he added. "Well, there are other hunters, but we don't know how many."

"Yeah and just to put the icing on the cake, little Sammy used to have to worry about being hunted himself sometimes. Whoops! I didn't mean to say that. Sorry Sam." Jo said. She put her face in her hands to hide her face that was red with embarrassment.

Skyler raised one eyebrow in question. "Why does Sam have to worry about being hunted?"

Dean glared at the back of Jo's head and then Sam, very calmly, started to explain. "Well you know that yellow-eyed demon that we were talking about before? Well a bunch of kids my age were born with psychic powers, like telekinesis and stuff like that, and when we were six months old, the demon came and visited our houses. Some of the kids mothers died that night because they walked in on us and the demon and us, but back to the point, that night we were given demon blood and the demon said that he was going to use all of us for an army. Really, he just wanted one of us, and apparently I won that prize, and now there are some hunters that would do anything to kill me."

"Wow, and I thought my life was complicated." Skyler said in a small voice.

Dean groaned and put his face in his hands. "I need a drink."


End file.
